US20220069233A1 - Compound, organic optoelectronic diode, and display device - Google Patents

Compound, organic optoelectronic diode, and display device Download PDF

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US20220069233A1
US20220069233A1 US17/418,728 US201917418728A US2022069233A1 US 20220069233 A1 US20220069233 A1 US 20220069233A1 US 201917418728 A US201917418728 A US 201917418728A US 2022069233 A1 US2022069233 A1 US 2022069233A1
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Mi Jin Kim
Jun tae Mo
Jong Su Lee
Ji Yoon BYUN
Yong Hui Lee
Dong Jun Kim
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LT Materials Co Ltd
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LT Materials Co Ltd
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H01L51/0052—
    • H01L51/0067—
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    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
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    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission

Definitions

  • a compound, an organic optoelectronic diode, and a display device are disclosed.
  • An organic optoelectronic diode is a diode that converts electrical energy into photoenergy, and vice versa.
  • An organic optoelectronic diode may be classified as follows in accordance with its driving principles. One is a photoelectric diode in which excitons generated by photoenergy, are separated into electrons and holes, and electrons and holes are transferred to different electrodes respectively to generate electrical energy, and the other is a light emitting diode where a voltage or a current is supplied to an electrode to generate photoenergy from electrical energy.
  • Examples of the organic optoelectronic diode may be an organic photoelectric diode, an organic light emitting diode, an organic solar cell, and an organic photoconductor drum.
  • organic light emitting diode (OLED) has recently drawn attention due to an increase in demand for flat panel displays.
  • the organic light emitting diode (OLED) converts electrical energy into light, and the performance of the organic light emitting diode (OLED) may be mainly affected by characteristics of organic materials located between the electrodes.
  • the organic light emitting diode has a structure in which an organic thin film is disposed between two electrodes.
  • a voltage is applied to the organic light emitting diode (OLED) having the structure, electrons and holes injected from the two electrodes combine with each other in an organic thin film to make a pair, and then emit light while being extinguished.
  • the organic thin film may be composed of a single layer or multilayers as necessary.
  • a material of the organic thin film may have a light emitting function as necessary.
  • the material for the organic thin film it is also possible to use a compound which may itself constitute a light emitting layer alone, or it is also possible to use a compound which may serve as a host or dopant of a host-dopant-based light emitting layer.
  • a material for the organic thin film it is also possible to use a compound which may perform a function such as hole injection, hole transport, electron blocking, hole blocking, electron transport, or electron injection.
  • An embodiment provides a compound for an organic optoelectronic diode capable or realizing an organic optoelectronic diode having high efficiency and long life span.
  • Another embodiment provides an organic optoelectronic diode including the compound.
  • Another embodiment provides a display device including the organic optoelectronic diode.
  • X 1 is —O— or —S—
  • Ar 1 is a substituent having electron characteristics or a substituent having hole characteristics
  • R 1 to R 6 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or a combination thereof,
  • L 1 is a single bond, a substituted or unsubstituted C6 to C60 arylene group, or a substituted or unsubstituted C2 to C60 heteroarylene group,
  • n1 is one of integers of 0 to 2
  • FuseR 1 and FusedR 2 are each independently a substituted or unsubstituted C3 to C60 fused ring.
  • an organic optoelectronic diode includes an anode and a cathode facing each other and at least one organic layer disposed between the anode and the cathode, wherein the organic layer includes the compound.
  • a display device including the organic optoelectronic diode is provided.
  • An organic optoelectronic diode having high efficiency and a long life span may be realized.
  • FIGS. 1 to 3 are each cross-sectional views showing organic light emitting diodes according to embodiments.
  • substituted or unsubstituted is substituted or unsubstituted with one or more substituents selected from the group consisting deuterium; a halogen; —CN; a C1 to C60 linear or branched alkyl group; a C2 to C60 linear or branched alkenyl group; a C2 to C60 linear or branched alkynyl group; a C3 to C60 monocyclic or polycyclic cycloalkyl group; a C2 to C60 monocyclic or polycyclic heterocycloalkyl group; a C6 to C60 monocyclic or polycyclic aryl group; a C2 to C60 monocyclic or polycyclic heteroaryl group; —SiRR′R′′; —P( ⁇ O) RR′; a C1 to C20 alkylamine group; a C6 to C60 monocyclic or polycyclic arylamine group; a C2 to C60 monocyclic
  • substituents can additionally form rings with adjacent substituents.
  • a substituent formed by linking two or more substituents may be a biphenyl group.
  • the biphenyl group may refer to an aryl group or a substituent to which two phenyl groups are linked.
  • the additional substituents may be further substituted.
  • R, R′, and R′′ are the same as or different from each other, and are each independently hydrogen; deuterium; —CN; a substituted or unsubstituted C1 to C60 linear or branched alkyl; a substituted or unsubstituted C3 to C60 monocyclic or polycyclic cycloalkyl group; a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aryl group; or a substituted or unsubstituted C2 to C60 monocyclic or polycyclic heteroaryl group.
  • the “substituted or unsubstituted” is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen, —CN, —SiRR′R′′, —P( ⁇ O)RR′, a C1 to C20 linear or branched alkyl group, a C6 to C60 monocyclic or polycyclic aryl group, and a C2 to C60 monocyclic or polycyclic hetero aryl group, and the R, R′, and R′′ are the same as or different from each other, and are each independently hydrogen, deuterium, —CN, a C1 to C60 alkyl group substituted or unsubstituted with deuterium, a halogen, —CN, a C1 to C20 alky group, a C6 to C60 aryl group, and a C2 to C60 hetero aryl group; a C3 to C60 cycloal
  • substituted refers to when a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is a position at which a hydrogen atom is substituted, that is, the position is not limited as long as the substituent can be substituted, when substituted with two or more, two or more substituents may be the same as or different from each other.
  • the halogen may be fluorine, chlorine, bromine, or iodine.
  • the alkyl group may include a C1 to C60 linear or branched chain, and may be further substituted by other substituents.
  • the carbon number of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20.
  • alky group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cylcopentylmethyl, cylcohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhe
  • the alkenyl group may include a C2 to C60 linear or branched chain, and may be further substituted by other substituents.
  • the carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.
  • alkenyl group examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, styrenyl, and the like, but are not limited thereto.
  • the alkynyl group may include a C2 to C60 linear or branched chain, and may be further substituted by another substituent.
  • the carbon number of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.
  • the cycloalkyl group may include a C3 to C60 monocyclic or polycyclic ring, and may be further substituted by another substituent.
  • the polycyclic ring refers to a group in which a cycloalkyl group is directly connected or condensed with another ring group.
  • the other ring group may be a cycloalkyl group, but may be another type of ring group, such as a heterocycloalkyl, an aryl, a heteroaryl, or the like.
  • the carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20.
  • the cycloalkyl group is cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.
  • the alkoxy group may be a C1 to C10 alkoxy group, and more specifically, may be methoxy, ethoxy, propoxy, butoxy, pentoxy, and the like.
  • the silyl group may be represented by —SiRR′R′′, and the definition of R is as described above. More specifically, the silyl group may be dimethylsilyl, diethylsilyl, methylethylsilyl, or the like.
  • the phosphine oxide group may be represented by —P( ⁇ O)RR′, and the definitions of R and R′ are as described above. More specifically, the phosphine oxide group may be a dimethyl phosphine oxide, a diethyl phosphine oxide, a methyl ethyl phosphine oxide, or the like.
  • the fluorenyl group refers to a substituent including various substituents at position 9.
  • the fluorenyl group may be used in a concept including a fluorenyl group substituted with two hydrogens, two alkyl groups, two aryl groups, or two heteroaryl groups at position 9. More specifically, the fluorenyl group may be a 9-di-H-fluorenyl group, a 9-di-methyl-fluorenyl group, a 9-di-phenyl-fluorenyl group, or the like.
  • the heterocycloalkyl group may include O, S, Se, N, or Si as a hetero atom, may include a C2 to C60 monocyclic or polycyclic ring, and may be further substituted by another substituent.
  • the polycyclic ring refers a group in which a heterocycloalkyl is directly connected or condensed with another ring group.
  • the other ring group may be a heterocycloalkyl group, but may be another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, or the like.
  • the carbon number of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.
  • the aryl group may include a C6 to C60 monocyclic or polycyclic ring, and may be further substituted by another substituent.
  • the polycyclic ring refers a group in which an aryl is directly connected or condensed with another ring group.
  • the other ring group may be an aryl group, but may be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, or the like.
  • the aryl group may include a spiro group.
  • the carbon number of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25.
  • aryl group examples include phenyl, biphenyl, triphenyl, naphthyl, anthryl, chrysenyl, phenanthrenyl, perylenyl, fluoranthenyl, triphenylenyl, phenalenyl, pyrenyl, tetrasenyl, pentacenyl, fluorenyl, indenyl, acenaphthylenyl, benzofluorenyl, spirobifluorenyl, 2,3-dihydro-1H-indenyl, and condensed rings thereof, or the like, but are not limited thereto.
  • the spiro group may include a spiro structure, and may be C15 to C60.
  • the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro bonded to a fluorenyl group.
  • the spiro group may include any one of following structural formulas.
  • the heteroaryl may include S, O, Se, N, or Si as a hetero atom, and may include a C2 to C60 monocyclic or polycyclic ring, and may be further substituted by other substituents.
  • the polycyclic ring refers a group in which a heteroaryl group is directly connected or condensed with another ring group.
  • the other ring group may be a heteroaryl group, but may be another type of ring group, such as a cycloalkyl group, an heterocycloalkyl group, an aryl group, or the like.
  • the carbon number of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25.
  • heteroaryl group examples include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thiophene, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, and triazolyl groups, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group, a thiazinyl group, a deoxyl group, a triazinyl group, a tetrazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group,
  • the amine group may be selected from the group consisting of: a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; —NH2; a dialkylamine group; a diarylamine group; a diheteroarylamine group; an alkylarylamine group; an alkylheteroarylamine group; and an arylheteroarylamine group, and the carbon number is not particularly limited, but is preferably 1 to 30.
  • heteroaryl group examples include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenyrenylamine group, a biphenyltriphenylenylamine group, or the like, but are not limited thereto.
  • an arylene group means one having two bonding positions, that is, a divalent group.
  • the description of the aryl groups described above may be applied except that they are each divalent.
  • a heteroarylene group means having two bond positions in a heteroaryl group, that is, a divalent group. The description of the heteroaryl group described above may be applied except that they are each divalent.
  • hole characteristics refer to an ability to donate an electron to form a hole when an electric field is applied, and that a hole formed in the anode may be easily injected into the light emitting layer and transported in the light emitting layer due to conductive characteristics according to a highest occupied molecular orbital (HOMO) level.
  • HOMO highest occupied molecular orbital
  • a substituted or unsubstituted C6 to C60 aryl group having hole characteristics a substituted or unsubstituted C2 to C60 heteroaryl group having hole characteristics, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heteroarylamine group may be used.
  • the substituted or unsubstituted C6 to C60 aryl group having the above hole characteristics may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted Spiro-fluorenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perrylenyl group, or a combination thereof.
  • the substituted or unsubstituted C2 to C60 heteroaryl group having the hole characteristics may be a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted indole carbazolyl group, and the like.
  • the aryl group or heteroaryl group which is a substituent bonded to the nitrogen of the substituted or unsubstituted arylamine group and substituted or unsubstituted heteroarylamine group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted
  • electron characteristics refer to an ability to accept an electron when an electric field is applied and that electrons formed in the cathode may be easily injected into the light emitting layer and transported in the light emitting layer due to conductive characteristics according to a lowest unoccupied molecular orbital (LUMO) level.
  • LUMO lowest unoccupied molecular orbital
  • the substituted or unsubstituted C2 to C60 heteroaryl group having electron characteristics may be a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted isofuranyl group, a substituted or unsubstituted benzoisofuranyl group, a substituted or unsubstituted oxazoline group, a substituted or unsubsti
  • substituted or unsubstituted C2 to C60 heteroaryl group having the above electron characteristics may be any one of the following formulas X-1 to X-5.
  • L n may be a direct bond (or a single bond), a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
  • L n may be a direct bond, a substituted or unsubstituted C6 to C60 arylene group, or a substituted or unsubstituted C2 to C60 heteroarylene group.
  • L n may be a direct bond, a substituted or unsubstituted C6 to C40 arylene group, or a substituted or unsubstituted C2 to C40 heteroarylene group.
  • the “n” in the L n means a number for distinguishing a substituent.
  • the compound according to an embodiment is represented by the following formulas.
  • X 1 may be —O—, or —S—
  • Ar 1 may be a substituent having electron characteristics or a substituent having hole characteristics
  • R 1 to R 6 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or a combination thereof, may be a single bond, a substituted or unsubstituted C6 to C60 arylene group, or a substituted or unsubstituted C2 to C60 heteroarylene group, n1 may be one of integers of 0 to 2, * may be a linking point of Formulas 1-1 and 2-1, and FuseR 1 and FusedR 2 may each independently be a substituted or unsubstituted C3 to C60 fused ring. More specifically, F
  • the compound is a structure in which at least one fused ring is formed in the carbazole core.
  • a dibenzofuranyl group or a dibenzothiophenyl group may be bonded to the core structure, and a substituent having electron characteristics or a substituent having hole characteristics may be further bonded.
  • the compound has high thermal stability because of the high glass transition temperature (Tg).
  • Tg glass transition temperature
  • Formula 1-1 may be represented by Formula 1-2.
  • X 1 may be —O— or —S—
  • Ar 1 may be a substituent having electron characteristics or a substituent having hole characteristics
  • R 5 and R 6 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or a combination thereof, may be a singly bond, a substituted or unsubstituted C6 to C60 arylene group, or a substituted or unsubstituted C2 to C60 heteroarylene group, n1 may be one of integers of 0 to 2, and * may be a linking point of Formula 1-2 and 2-1.
  • Formula 1-2 specifically describes the binding position, considering the ease of synthesis and the efficiency of the expansion of the electron cloud.
  • Formula 2-1 may be represented by Formula 2-2.
  • R 1 to R 4 may be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or a combination thereof, and * may be a linking point of Formula 1-1 and 2-2.
  • Formula 2-1 may be represented by Formula 2-3.
  • R 1 to R 4 and R 7 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or a combination thereof, and * may be a linking point of Formula 1-1 and 2-3.
  • Formula 2-1 may be represented by Formula 2-4.
  • R 1 to R 4 may be each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or a combination thereof, and * may be a linking point of Formula 1-1 and 2-4.
  • Formula 2-1 may be represented by Formula 2-5.
  • R 1 to R 4 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or a combination thereof, and * may be a linking point of Formula 1-1 and 2-5.
  • Formula 2-1 may be represented by Formula 2-6.
  • R 1 to R 4 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or a combination thereof, and * may be a linking point of Formula 1-1 and 2-6.
  • Formula 2-1 may be represented by Formula 2-7.
  • R 1 to R 4 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or a combination thereof, and * may be a linking point of Formula 1-1 and 2-7.
  • Formula 2-1 may be represented by Formula 2-8.
  • R 1 to R 4 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or a combination thereof, and * may be a linking point of Formula 1-1 and 2-8.
  • Formula 2-1 may be represented by Formula 2-9.
  • R 1 to R 4 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or a combination thereof, and * may be a linking point of Formula 1-1 and 2-9.
  • Formula 2-1 may be represented by Formula 2-10.
  • R 1 to R 4 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or a combination thereof, and * may be a linking point of Formula 1-1 and 2-10.
  • Formula 2-1 may be represented by Formula 2-11.
  • R 1 to R 4 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or a combination thereof, and * may be a linking point of Formula 1-1 and 2-11.
  • the carbazole cores of Formulas 2-2 to 2-11 may be selected in consideration of a substituent additionally bonded to the compound.
  • the various carbazole structures can satisfy the thermal stability and various energy levels of the compound.
  • the Ar 1 may be a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group.
  • the Ar 1 may be the following Formula 3-1 or Formula 3-2.
  • the X 1 to X 3 may be —CR′—, or —N—, at least one of X 1 to X 3 may be —N—, Ar 2 and Ar 3 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or a combination thereof, and R′ may be hydrogen, deuterium, a cyano group, or a substituted or unsubstituted C1 to C60 alkyl group.
  • At least one of Ar 2 and Ar 3 may be any one of Formula 4-1 to Formula 4-5.
  • X may be —NR x —, —O—, —S—, or —CR x R y —
  • R x and R y may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, or a C6 to C60 aryl group
  • R b to R e may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, or a C6 to C60 aryl group.
  • the R 1 to R 6 may each independently be any one of substituents of the following Group I.
  • * may be a linking point.
  • the compound of one example described above may be represented by any one of the compounds of Group II.
  • the compound or composition described above may be for an organic optoelectronic diode, and the compound for an organic optoelectronic diode or composition for an organic optoelectronic diode may be formed by dry film formation such as chemical vapor deposition.
  • the organic optoelectronic diode is not particularly limited as long as it is a diode that converts electrical energy into light energy, and vice versa, and examples thereof include an organic photoelectric diode, an organic light emitting diode, an organic solar cell, and an organic photoconductor drum.
  • the organic emitting diode includes: the first electrode; the second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein the one or more organic material layers provide the organic emitting diode including the heterocyclic compound represented by Formula 1.
  • the first electrode may be an anode
  • the second electrode may be a cathode
  • the first electrode may be a cathode
  • the second electrode may be an anode
  • the organic light emitting diode may be a blue organic light emitting diode, and the heterocyclic compound according to Formula 1 can be used as a material of the blue organic light emitting diode.
  • the organic light emitting diode may be a green organic light emitting diode, and the heterocyclic compound according to Formula 1 can be used as a material of the green organic light emitting diode.
  • the organic light emitting diode may be a red organic light emitting diode, and the heterocyclic compound according to Formula 1 can be used as a material of the red organic light emitting diode.
  • the organic light emitting diode of the present invention may be manufactured by a method and with materials for manufacturing a conventional organic light emitting diode, except that one or more organic material layers are formed using the heterocyclic compound described above.
  • the heterocyclic compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting diode.
  • the solution coating method may be spin coating, dip coating, inkjet printing, screen printing, a spray method, roll coating, and the like, but is not limited thereto.
  • FIGS. 1 to 3 illustrate a lamination order of electrodes and organic material layers of an organic light emitting diode according to one embodiment of the present application.
  • an organic light emitting diode in which an anode 200 , an organic material layer 300 , and a cathode 400 are sequentially laminated on a substrate 100 is illustrated.
  • an organic light emitting diode in which a cathode 400 , an organic material layer 300 , and an anode 200 are sequentially laminated on a substrate 100 may be provided.
  • FIG. 3 illustrates a case where the organic material layer is a multilayer.
  • An organic light emitting diode may include a hole injection layer 301 , a hole transport layer 302 , a light emitting layer 303 , a hole blocking layer 304 , an electron transport layer 305 , and an electron injection layer 306 .
  • the scope of the present application is not limited by such a laminated structure, and other layers except for the light emitting layer may be omitted, and other functional layers may be added as needed.
  • the compound represented by Formula 1 may be used as an electron transport layer, a hole transport layer, or a light emitting layer in an organic light emitting diode.
  • anode material materials having a relatively large work function may be used, and a transparent conductive oxide, a metal, or a conductive polymer may be used.
  • anode material examples include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO; Al or SnO 2 ; combinations of oxides with metals such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole, polyaniline, and the like, but are not limited thereto.
  • metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof
  • metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO; Al or SnO 2 ; combinations of oxides with metals such as Sb
  • conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,
  • cathode material materials having a relatively low work function may be used, and metals, metal oxides, or conductive polymers may be used.
  • cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structural materials such as LiF/Al, LiO 2 /Al; and the like, but are not limited thereto.
  • hole injection materials may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429, or a starburst type of amine derivative such as tris(4-carbazoyl)-9-ylphenyl)amine (TCTA), 4,4′,4′′-tri[phenyl (m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB) disclosed in [Advanced Material, 6, p.
  • TCTA tris(4-carbazoyl)-9-ylphenyl)amine
  • m-MTDATA 4,4′,4′′-tri[phenyl (m-tolyl)amino]triphenylamine
  • m-MTDAPB 1,3,5-tris[4-(3-methylphenylphenylamino)pheny
  • a soluble conductive polymer such as polyaniline/dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate), polyaniline/camphor sulfonic acid, polyaniline/poly(4-styrenesulfonate), and the like.
  • hole transport material pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like may be used, and low molecular or high molecular materials may be used.
  • metal complexes of oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinomethane and derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinoline and derivatives thereof, and the like may be used, and high molecular materials as well as low molecular materials may be used.
  • LiF is representatively used in the art, but the present application is not limited thereto.
  • red, green, or blue light emitting materials may be used, and if necessary, two or more light emitting materials may be mixed and used.
  • two or more light emitting materials may be deposited by separate sources, or premixed and deposited by one source.
  • fluorescent materials may be used as the light emitting materials, it can also be used as phosphorescent materials.
  • materials which combine holes and electrons respectively injected from the anode and the cathode to emit light may be used, but materials in which both the host material and the dopant material are involved in light emitting may be used.
  • hosts of the same type may be mixed and used, or hosts of different types may be mixed and used.
  • n-type host materials and p-type host materials may be used as the host materials of the light emitting layers.
  • the organic light emitting diodes according to the exemplary embodiment of the present application may be top emission types, bottom emission types, or double-sided emission types according to materials used.
  • the main mechanism is as follows.
  • the objective compound P2 was obtained from the mixture by extracting with MC and water, drying with MgSO 4 , and separating through silica gel column chromatography.
  • the objective compound P1 was obtained from the mixture by extracting with MC and water, drying with MgSO 4 , and separating through silica gel column chromatography.
  • the prepared compound was confirmed from Mass results.
  • ITO indium tin oxide
  • the glass substrate was ultrasonic wave-washed with a solvent such as acetone, methanol, isopropyl alcohol, and the like and dried, and then the glass substrate was UVO treated for 5 minutes using UV in a UV cleaner.
  • a solvent such as acetone, methanol, isopropyl alcohol, and the like
  • the substrate was moved to a plasma cleaner (PT), and then plasma-treated in a vacuum atmosphere to remove the ITO work function and residual film, and moved to a thermal depositor for organic deposition.
  • PT plasma cleaner
  • 2-TNATA(4,4′,4′′-tris[2-naphthyl(phenyl)amino] triphenylamine) as the hole injection layer and NPB(N,N′-di(1-naphthyl)-N,N′-diphenyl-(1,1-biphenyl)-4,4′-diamine) as a hole transport layer were formed as common layers.
  • the light emitting layer was deposited thereon by thermal evaporation as follows.
  • a 500 ⁇ -thick light emitting layer was deposited by doping 3% (piq) 2 (Ir)(acac) to the host, using a compound shown in the table below as a red host, and using (piq) 2 (Ir)(acac) as a red phosphorescent dopant.
  • LiF lithium fluoride
  • Al aluminum
  • the electroluminescence (EL) characteristics of the organic electroluminescent diode manufactured as described above were measured by the Mcscience M7000 system. And the T90 was measured when the reference luminance was 6,000 cd/m 2 from the EL measurement result using a life span measuring instrument (M6000) manufactured by Mcscience.
  • M6000 life span measuring instrument
  • the examples when the material using dibenzofurane which is a linker of the compound of the present invention is used as the red light emitting layer host, in the organic light emitting diode, the examples have a lower driving voltage, and significantly improved efficiency and life span compared to Comparative Examples A to G.
  • the dibenzofurane linker is introduced between Sub A and Sub B of a compound to manufacture the compound having a suitable bandgap as the red host, and the compound can satisfy the requirements of the light emitting layer.
  • the electron transfer capability is improved, resulting in an excellent effect on driving and efficiency, while also improving thermal stability and life span properties.
  • the compounds have improved driving, efficiency, and life span, compared to the structure in which Sub B is directly bonded to N of carbazole (Sub A) without a linker (Comparative Example A, Comparative Example B).

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